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Inhibition of indoleamine 2,3-dioxygenase and tryptophan 2,3-dioxygenase by beta-carboline and indole derivatives

Arch Biochem Biophys. 1984 Aug 1;232(2):602-9. doi: 10.1016/0003-9861(84)90579-4.

Abstract

beta-Carboline derivatives inhibited both indoleamine 2,3-dioxygenase and tryptophan 2,3-dioxygenase activities from various sources. Among them, norharman is most potent for both enzymes from mammalian sources. Kinetic studies revealed that norharman is uncompetitive (Ki = 0.12 mM) with L-tryptophan for rabbit intestinal indoleamine 2,3-dioxygenase, and linearly competitive (Ki = 0.29 mM) with L-tryptophan for mouse liver tryptophan 2,3-dioxygenase. In addition, some beta-carbolines selectively inhibited one enzyme or the other. Pseudomonad tryptophan 2,3-dioxygenase was inhibited by a different spectrum of beta-carbolines. Such a selective inhibition by the structure of substrate analogs is more evident by the use of indole derivatives. Indole-3-acetamide, indole-3-acetonitrile and indole-3-acrylic acid exhibited a potent inhibition for mammalian tryptophan 2,3-dioxygenase, while they moderately inhibited the pseudomonad enzyme. However, they showed no inhibition for indoleamine 2,3-dioxygenase. These results suggest the difference of the structures of the active sites among these enzymes from various sources.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Binding, Competitive
  • Carbolines / pharmacology*
  • Harmine / analogs & derivatives
  • Harmine / pharmacology
  • In Vitro Techniques
  • Indoles / pharmacology*
  • Intestine, Small / enzymology
  • Kinetics
  • Liver / enzymology
  • Mice
  • Oxygenases / antagonists & inhibitors*
  • Pseudomonas fluorescens / enzymology
  • Rabbits
  • Rats
  • Structure-Activity Relationship
  • Tryptophan Oxygenase / antagonists & inhibitors*

Substances

  • Carbolines
  • Indoles
  • Harmine
  • Oxygenases
  • Tryptophan Oxygenase